Helping [M]y much older coworker [F] celebrate her birthday

Dana and I had been coworkers for a couple of years when this story takes place. I was 21 and she was just turning 43. And to be honest, she was WAY out of my league.

Physically speaking, Dana was around 5’4″-5’5″ with medium short dark brown hair and green eyes. Her face closely resembles the actress Mena Suvari, if you’re familiar. And body wise, Dana was on the thick side. Not a BBW, but thick. Her breasts weren’t huge, a small C cup at most, but her ass was out of this world! Like the true definition of a badonkadonk.

As far as our work relationship went, we got along great. She was an office worker and I was a blue collar guy, but we shared the same break area and would often talk during lunch. I had developed a bit of a crush on her and as time went on I got a little bolder.

I was young and dumb and as such I became a huge flirt. Dana, however, just laughed off all my advances telling me more than once that I was too young. Still, though, we remained friendly.

One day we were on break, just the two of us, and she let it slide that her birthday was the following day, a Saturday. In my typical (at that time) corny flirty manner, I wished her an early happy bday and asked if she had a hot date for her birthday. And to my utter shock she replied almost immediately “no, why? You want to be my hot date?”

“Uh, yeah!” I replied, quickly recovering and offering to take her out to dinner. She agreed and wrote her number down on a napkin and we made plans to meet up the next evening around 8pm.

I couldn’t believe it. I finally got a date with Dana, the sexy older woman I had been fantasizing about for two years! And guess what?

I canceled.

Yep. Stupid, huh? I got nervous. Scared. Called her and made an excuse, offering to take her out another time.

The more I thought about it the more I realized how much I screwed up, though. I finally came to my senses later that night, manned up, and called her again.

I said I’m suddenly free and that, if she wanted,I could stop by her place and hang out. To which Dana readily agreed, giving me her address.

30 minutes later I was there, on her couch as we drank wine and searched for a movie to watch. And believe it or not we actually watched the entire movie! (It was 28 Days Later, FYI)

Finally the credits roll. At this point we’re both slightly buzzed from the wine and we’re just talking and joking. And, much to my delight, Dana is becoming a little handsy. At one point she even playfully slapped me on the ass when we were in the kitchen getting refills!

The more we talked, the closer we got on the couch. Finally we came to one of those awkward moments. You know the type…neither of you speaking, just looking at each other, faces mere inches away…

So, I went for it. Leaned in for a kiss. A kiss that Dana returned, and then some.

It started slow, our lips just grazing before gently probing each others mouths, tongues softly playing.

I lost track of time. I honestly don’t know how long we spent making out on the couch. It could have been five minutes or it could have been over half an hour. But we both became more aggressive. She moaned into my mouth as our hands roamed each others bodies, over our clothes. I began kissing her neck, her ear lobes, her throat.

Finally she pulled back and asked if I’d like to go to the bedroom. When I replied that I would, she stood and took me by the hand, leading me down a hall.

Stopping abruptly Dana turned to face me, a serious look on her face. “You can’t tell anyone at work about this!”

“I won’t”

“You promise?”

“I promise”

With that assurance she took me to her room, and into her bed.

A quick note about Dana. She was a widow. And, despite being just 43, already a grandmother. Her two daughters were already grown. One was a couple of years older than me and the other a year younger.

I would soon find out that this was her first time with a man in 4 years. I was her first since her husband passed. I didn’t know this until after everything was said and done, though.

Once in her bedroom, we both unceremoniously stripped down as quickly as possible and jumped up on her big king size bed.

And Dana’s body was amazing. So perfectly soft. Her skin tanned a golden color all over. Wide hips spread as I laid her back, revealing a full bush. This was a first for me, being with a woman that didn’t shave her pussy. I was undeterred though and quickly kissed my way down until my face was firmly between her thighs.

She stopped me, though. Almost as soon as I began.

“Just lay back” she ordered.

I did as I was told and Dana straddled me, raising herself up as she took my cock in her free hand. Slowly lowering herself down on it.

And I do mean slowly. What happened next is surreal and I’ve still yet to experience anything quite as intense.

As she lowered herself down, she reached down and took my hands and placed them on her breasts. Then she slowly began rocking back and forth.

I cupped her tits, ran my thumbs over her large erect nipples, and began thrusting up into her.

Within less than two minutes Dana began moaning. A strange, deep moan. And she began freezing up. She’d tense up, moan as if in pain, shudder, then tense up again.

I actually thought I was hurting her! I asked if she was ok as she moaned out yes and continued to shudder and writhe on top of me.

By this point I began to lose control as well. I began thrusting faster and we soon found a rhythm just before I exploded, my bare cock emptying itself inside her.

A moment later she collapsed on top of me, her head on my chest. My cock still inside her, still semi hard.

We laid there like that for about ten minutes, recovering, before Dana got up and went to the restroom. She returned with a warm wet towel that she used to wipe my crotch down with. It felt fucking amazing.

That’s when she told me I was her first in 4 years. I couldn’t believe it. Hell, I couldn’t believe any of it. I actually pinched myself at one point. I couldn’t believe I was laying in bed with my literal fantasy woman next to me.

We fucked twice more that night, both times lasted much longer than the first session and both resulted in both of us having orgasms, but neither was as intense as that first fuck.

And our fling lasted about 3 months. I scratched an itch, for sure, but she needed more. True love. Besides, it was hard keeping it a secret from our other coworkers.

Dana was one of those lucky women who cum from penetration and she really wasn’t much for foreplay. She loved to kiss and was a great kisser, but when it came to fucking she just wanted the dick. She never went down on me and I never attempted to go down on her again.

I also never wore a condom with Dana. Call me stupid, yeah…I know. It just felt so perfectly natural. She had previously had a hysterectomy so there was no worries about pregnancy.

I’ll never forget our very last time together, though. It was the only time I didn’t cum inside her.

It was doggy style, with me standing. Her ass was in the air and she was backed up to the foot of the bed. That amazing ass just bouncing back against me as I stroked my cock back and forth. Deeper and harder, both hands gripping her hips, my fingers digging in.

She began moaning deep, that same gutteral moan I had become accustomed to. Things were so hot and heavy, and as a result – wet, that I slipped out. My cock landing on her big soft ass.

The sight of my cock, throbbing and hard and wet with her juices, against her big mature ass cheeks, was just too much and I came immediately. Ropes of my young hot cum all over her ass.

I can still see it in my mind to this day.

Source: reddit.com/r/gonewildstories/comments/slupzs/helping_my_much_older_coworker_f_celebrate_her